Windermere Florida Homes for Sale

Discover Windermere, Florida: Where Luxury Meets Lake Life

Welcome to Windermere, one of Central Florida’s most prestigious and picturesque communities. Nestled among pristine lakes and rolling hills just 20 minutes from downtown Orlando, Windermere offers an exclusive blend of natural beauty, top-rated schools, and small-town charm that’s increasingly rare in the Sunshine State.

Known for its stunning lakefront estates and tree-lined streets, Windermere has become the address of choice for professionals, families, and those seeking a refined Florida lifestyle. The town’s unique character is defined by its 21 sparkling lakes, including the expansive Butler Chain of Lakes, which provide residents with world-class boating, fishing, and watersports opportunities right in their backyard.

Award-Winning Education

Families are drawn to Windermere’s exceptional educational opportunities. The area is served by highly-rated Orange County Public Schools, including Windermere Elementary and Windermere High School, both consistently earning “A” ratings. The Windermere Preparatory School, a prestigious private institution, offers world-class education from pre-K through 12th grade with an international focus.

Community & Lifestyle

Despite its growth, Windermere maintains its welcoming community spirit. The town center features charming local shops, restaurants, and the beloved town of Windermere hosts regular events throughout the year, including seasonal festivals and the popular farmers market. Residents enjoy easy access to world-renowned theme parks, while the nearby Orange County Parks system offers countless outdoor recreation opportunities.

Whether you’re seeking a waterfront estate, a family-friendly neighborhood, or a luxury golf course community, Windermere delivers an unparalleled Central Florida living experience. At Holiday Realty Florida, we’re proud to help you find your perfect home in this exceptional lakeside paradise.

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10506 Down Lakeview Cir, Windermere, Florida 34786

Residential For Sale

LA ROSA REALTY LLC
Under contract-accepting backup offers. Welcome Home to “The Lakes” — Windermere’s Hidden Gem Tucked away in the ultra-private The Lakes community of Windermere, this beautiful residence sits on a rare 1-acre lot with breathtaking views of Lake Down, part of the renowned Butler Chain of Lakes. With just 60 homes in the entire neighborhood, exclusivity and serenity come standard.
$1,350,000
4Bedroom(s)
3Bathroom(s)
Converted GarageParking(s)
3,888Sqft

11021 Hawkshead Ct, Windermere, Florida 34786

Residential For Sale

ALL REAL ESTATE & INVESTMENTS
Welcome to this exquisite 5-bedroom, 4-bathroom residence nestled on a premium corner lot in one of Windermere’s most beautiful, gated communities. Boasting 3,557 square feet of thoughtfully designed living space, this Spanish Colonial-style home blends timeless elegance with modern comfort.
$1,299,000
5Bedroom(s)
4Bathroom(s)
3,557Sqft

11334 Camden Loop Way, Windermere, Florida 34786

Residential For Sale

KEENE'S POINTE REALTY
Welcome to this beautifully refreshed single-story ranch in the desirable guard-gated community of Keene’s Pointe! Move-in ready and thoughtfully updated, this home features new luxury vinyl flooring, modern light fixtures, fresh interior and exterior paint, and a brand-new roof (2024). The oversized 3-car garage, complete with newly painted floors, provides abundant storage.
$1,295,000
4Bedroom(s)
3Bathroom(s)
3,021Sqft

11721 Camden Park Dr, Windermere, Florida 34786

Residential For Sale

COMPASS FLORIDA LLC
Under contract-accepting backup offers. Keene’s Pointe offers exceptional variety, with values that reflect each home’s design and level of renovation. This fully updated 4-bedroom, 3-bath home has been carefully reimagined and is now competitively priced to meet current market realities. The seller is motivated and ready to collaborate with buyers for a smooth closing.
$1,295,000
4Bedroom(s)
3Bathroom(s)
DrivewayParking(s)
3,014Sqft

3417 Bay Meadow Ct, Windermere, Florida 34786

Residential For Sale

ON ME REALTY
Fully renovated modern residence on a spacious 1-acre lot, featuring a brand-new contemporary kitchen with custom cabinetry, quartz countertops, and high-end appliances. This 4-bedroom home offers 4 full bathrooms, expansive living areas with soaring ceilings, and oversized porcelain tile flooring throughout.
$1,280,000
4Bedroom(s)
4Bathroom(s)
2,681Sqft

11318 Fenimore Court Ct, Windermere, Florida 34786

Residential For Sale

FSM REALTY INVESTMENTS
Welcome to 11318 Fenimore Ct, where a beautiful home awaits. This fully upgraded residence boasts four spacious bedrooms and three luxurious bathrooms, nestled on an expansive cul-de-sac lot overlooking a serene pond in Keene’s Pointe. Experience the joy of luxury living within a 24-hour, man-gated community nestled in the renowned Windermere.
$1,279,000
4Bedroom(s)
3Bathroom(s)
Garage Door OpenerParking(s)
2,523Sqft

2828 Ingeborg Ct, Windermere, Florida 34786

Residential For Sale

ALIGN REAL ESTATE LLC
Welcome to this Mediterranean dream home tucked away at the end of a quiet cul-de-sac in Windermere, just steps from beautiful Lake Down. Sitting on over an acre of fenced land, this property is one of the most unique opportunities in the area.
$1,275,000
5Bedroom(s)
5Bathroom(s)
Garage Door OpenerParking(s)
3,190Sqft

11357 Preserve View Drive, Windermere, Florida 34786

Residential For Sale

M2M REALTY
Perfectly located on a corner lot in highly desirable Keenes Pointe. This luxury 24-hour GUARD-GATED community features fitness, swimming, tennis, golf, and dinning, and the option to join Golden Bear Club with its Jack Nicklaus designed course and luxurious clubhouse (additional membership fee required). Close to shopping, restaurants and minutes from Disney.
$1,259,000
4Bedroom(s)
4Bathroom(s)
3,196Sqft

109 E 12th Ave, Windermere, Florida 34786

Residential For Sale

EXECUTIVE PROPERTIES
Modern upgrades meet timeless Windermere charm in this fully reimagined four-bedroom, three-and-a-half-bath home, just steps from Lake Bessie. Set on a beautifully manicured corner lot with no HOA, this thoughtfully updated property blends luxury, comfort, and functionality in one of Central Florida’s most desirable communities.
$1,244,000
4Bedroom(s)
4Bathroom(s)
Garage Door OpenerParking(s)
2,791Sqft

1250 Belfiore Way, Windermere, Florida 34786

Residential For Sale

CORCORAN PREMIER REALTY
Under contract-accepting backup offers. Imagine waking up each morning to sparkling water views—the pond and fountain glistening just beyond the window. That’s the lifestyle waiting for you in this Windermere luxury home inside the exclusive gated community of Tuscany Ridge. Step inside and discover the perfect balance of timeless elegance and everyday comfort.
$1,225,000
5Bedroom(s)
5Bathroom(s)
4,175Sqft

14238 Crest Palm Ave, Windermere, Florida 34786

Residential For Sale

OLYMPUS EXECUTIVE REALTY INC
Under Construction. Sample Image Experience the perfect blend of elegance, comfort, and practicality with this beautifully crafted new home in Windermere. Every element of this residence has been thoughtfully designed to create a space that feels both luxurious and inviting.
$1,222,740
6Bedroom(s)
4Bathroom(s)
Garage Door OpenerParking(s)
4,222Sqft

14389 Crest Palm Ave, Windermere, Florida 34786

Residential For Sale

OLYMPUS EXECUTIVE REALTY INC
One or more photo(s) has been virtually staged. Step into your next home at Palms at Windermere with the stunning Sweetwater floor plan. Offering over 4,400 square feet, this spacious two-story design features 6 bedrooms and 4.5 baths, blending luxury and function for today’s lifestyle. The first-floor owner’s suite is a private retreat with dual walk-in closets and a spa-inspired bath.
$1,204,835
6Bedroom(s)
5Bathroom(s)
Garage Door OpenerParking(s)
4,443Sqft
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